Considering a High-Level Career Pivot? Ask Yourself These 3 Questions First

You’re the Director of Finance at a prominent tech company, a position you’ve worked toward for years. Throughout the course of your career, you’ve strategically built your finance résumé and cultivated strong business relationships.

But now your company’s executives have offered you the option to shift into a non-finance role, perhaps Chief of Staff or Director of Investor Relations. You’ve reached an inflection point in your career. Do you continue climbing the ladder in finance? Or do you pivot into a new area?

First, let me congratulate you. The fact that you have this option proves you’ve achieved a high level of success. Your company recognizes that you can add value in different ways, and they’re opening new doors for you. This is a milestone in your career.

However, these new opportunities might bring up some uncertainty. I’ve met with many people who have reached this point in their career and are now wondering, “What should I do? I’ve spent my entire professional life in this one area. Do I continue down that path? Or do I try something different?”

The answer differs from person to person. When you’ve reached this level of success, your next steps should be based on your unique aspirations. No one can decide for you. But I can offer you a framework for finding the right answer.

Reflecting on the following questions will help you determine which path is right for you.

Where Do I Ultimately Want to Be?

If you’re receiving offers to pivot within your company, you have a proven track record, great relationships, and an admirable reputation. Now it’s time to think about the end game. What do you want to be the pinnacle of your career?

I know it can feel a little strange to think this way at first. But this is the fork in the road that will take you to that ultimate goal, so it’s important to choose wisely.

Perhaps you began your career intending to one day become a CFO. Is that still your dream? Or has that desire waned as you’ve gained experience in the field? Maybe you’d prefer to be in the business instead of pursuing the C-Suite.

The advice I offer anyone in this position is, “Begin with the end in mind.” Once you know your ultimate destination, think about the skill sets and experiences you’ll need to get there. By now, you’ve been with your company long enough to know all the key players and what each department does. That’s valuable information when making this decision.

Consider factors such as: What skills do I need to gain? Who do you want to work with? Who will help you cultivate the skills needed to get where you want to go? Which types of projects will provide the experience and visibility to take you to the next level? Which role will propel you forward?

Let’s assume you are interested in eventually becoming CFO. Moving from finance into a high level operations role could make sense as today’s CFO’s are very strategic and business minded, so this experience would add to your skill set in your ultimate pursuit. However, if you’re interested in becoming COO, taking an additional step upward in finance won’t add as much value. You’re better off pursuing a more strategic position so you can hone those traits.

Why Do I Want to Do This?

Before you commit to a new role, ask yourself why you’ve chosen this road, especially if you’re shifting to a new competency. Be brutally honest with yourself. Is this purely your decision? Or are you being swayed by other people’s opinions or expectations of what you should do?

As much as possible, don’t let political pressure affect your choice. The executive team may have their own agenda for you, and you don’t want to get on their trajectory unless it aligns with your goals. Be a team player, but not at the expense of your interests.

At this point in your career, change can be exciting and invigorating – but it’s also quite challenging. And if you set yourself down an unfamiliar course, it can be difficult to turn around.

While you might hear, “you can always go back,” this is not necessarily a given. If you’re unhappy in your new path and decide you want to return to your previous job, you might find you’ve mentally outgrown it (assuming it’s still available in the first place.) Thus, the only path forward is to continue in your new endeavor or to embark on yet another change. Alternatively, depending upon how much time you’ve spent on new endeavors, returning can be difficult because your skills might have grown a little stale.

None of these things are insurmountable, but it’s important to considering all the angles before making a major, life-changing career decision.

There are no rewards without risks, so don’t let fear deter you from making the more challenging decision. Just make sure this is your own True North — not someone else’s idea of what your True North should be.

Do I Have Realistic Expectations?

Now that you’re clear on where you want to go, make sure you have the support — both internal and external — to get there. You’ll need mental fortitude to navigate a new department and career path, especially in the beginning.

No matter how much you prepare intellectually before making the shift, you’ll encounter curveballs and surprises left and right. Make sure you’re prepared to meet those with patience, humility, and resilience.

Ask your colleagues, friends, and family for support during this transition. Explain why you’ve made this decision, and share your goals and fears with them. Let them know how they can best help you. You are bound to be uncomfortable during a major career change, and support from those who know you best can make all of difference in the world.

Whatever you need from your community during this pivot, ask for it.

Be clear about how your lifestyle will change as well. You may earn less money for a while, so you’ll have to cut back on dining out and other small luxuries. Perhaps you have to travel more for work, which may force you to scale back on social commitments. Assess what this change means for every area of your life. The more prepared you and your family are ahead of the transition, the happier and more successful you’ll be once you take the leap.

The opportunity to pivot in your career is a gift. Mid-career professionals often assume time has passed them by and that it’s too late to try something new. But you can pursue new dreams at any age and under any circumstances.

The key is to understand why you’re seeking a new path and to know you’re doing it for the right reasons. If your expectations are realistic and you have the support of your family and peers, there’s no limit to what you can achieve in this new stage of your professional life.